Synthesis and properties of new aromatic poly(amine‐imide)s derived from <i>N,N</i>′‐bis(4‐aminophenyl)‐<i>N,N</i>′‐diphenyl‐1,4‐phenylenediamine

Liou, Guey‐Sheng; Hsiao, Sheng‐Huei; Ishida, Mina; Kakimoto, Masa–aki; Imai, Yoshio

doi:10.1002/pola.10430

Cited by 60 publications

(29 citation statements)

References 18 publications

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“…One of the common approaches for increasing the solubility and processability of polyamides and polyimides without sacrificing their high thermal stability is the introduction of bulky, packing‐disruptive groups and/or kink structures into the polymers 30–40. Recently, we reported the synthesis of soluble aromatic polyamides and polyimides bearing TPA units in the main chain based on N,N ′‐bis(4‐aminophenyl)‐ N,N ′‐diphenyl‐1,4‐phenylenediamine,41, 42 N,N ‐bis(4‐aminophenyl)‐ N ′, N ′‐diphenyl‐1,4‐phenylenediamine 43, 44. and N,N ‐bis(4‐carboxyphenyl)‐ N ′, N ′‐diphenyl‐1,4‐phenylenediamine 45, 46.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of photoluminescent and electrochemical properties of new aromatic polyamides and polyimides with a kink 1,2‐phenylenediamine moiety

Liou

Yang

2006

J. Polym. Sci. A Polym. Chem.

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A series of novel triphenylamine‐containing aromatic polyamides and polyimides having a crank and twisted noncoplanar structures were synthesized in inherent viscosities of 0.14–0.64 dL/g and 0.11–0.67 dL/g, respectively. These polymers had useful levels of thermal stability associated with relatively high glass‐transition temperatures (174–311 °C). They exhibited strong UV–Vis absorption bands at around 300 nm in NMP solutions. The PL spectra of these polymers in NMP solutions (1 × 10−5 M) showed maximum peaks around 396–479 nm. The hole‐transporting and electrochromic properties were examined by electrochemical and spectroelectrochemical methods. Cyclic voltammetry (CV) of the polymer films cast onto an indium‐tin oxide (ITO)‐coated glass substrate exhibited two reversible oxidation redox couples at potentials of 0.70–1.01 V and 1.10–1.46 V, respectively, vs. Ag/AgCl in acetonitrile solution. The polymer films revealed electrochromic characteristics, with a color change from neutral pale yellowish to green and then to a blue oxidized form at applied potentials ranging from 0.00 to 1.75 V. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 2587–2603, 2006

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Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of photoluminescent and electrochemical properties of new aromatic polyamides and polyimides with a kink 1,2‐phenylenediamine moiety

Liou

Yang

2006

J. Polym. Sci. A Polym. Chem.

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“…Thus, a number of novel PAIs have been readily prepared using this convenient technique by our laboratory 29. Recently, the synthesis of soluble aromatic polyamides and polyimides bearing triphenylamine units in the main chain based on N , N ′‐bis(4‐aminophenyl)‐ N , N ′‐diphenyl‐1,4‐phenylenediamine,30,31 N , N ‐bis(4‐aminophenyl)‐ N ′, N ′‐diphenyl‐1,4‐phenylenediamine,32,33 N , N ′‐bis(4‐carboxyphenyl)‐ N , N ′‐diphenyl‐1,4‐phenylenediamine,34 and N , N ‐bis(4‐carboxyphenyl)‐ N ′, N ′‐diphenyl‐1,4‐phenylenediamine,35 respectively, have been reported. Because of the incorporation of bulky, propeller‐shaped triphenylamine units along the polymer backbone, all the polymers are amorphous, show good solubility in many aprotic solvents, good film‐forming capability, and exhibit high thermal stability.…”

Section: Introductionmentioning

confidence: 99%

Poly(amine‐amide‐imide)s Bearing Pendent N‐Carbazolylphenyl Moieties: Synthesis and Electrochromic Properties

Liou

Chen

Yen

2006

Macro Chemistry & Physics

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Summary: A series of novel poly(amine-amide-imide)s with pendent N-carbazolylphenyl units that have inherent viscosities of 0.45-0.66 dL Á g À1 are prepared from various aromatic bis(trimellitimide)s and the new carbazole-based aromatic diamine, 4,4 0 -diamino-4 00 -N-carbazolyltriphenylamine, by direct polycondensation. All the polymers are readily soluble in polar organic solvents. Flexible, amorphous, and deep reddish films of poly(amine-amide-imide)s can be obtained by solution casting, and have useful levels of thermal stability associated with high glass transition temperatures (307-343 8C), 10% weight-loss temperatures in excess of 500 8C, and char yields at 800 8C in nitrogen higher than 65%. These polymers exhibit a maximum UV-vis absorption at 300 nm with a fluorescence emission maxima around 449-454 nm in N-methyl-2-pyrrolidinone solution. The hole-transporting and electrochromic properties are examined by electrochemical and spectroelectrochemical methods. Cyclic voltammograms of the poly(amine-amideimide) films cast onto an indium tin oxide-coated glass substrate exhibit a reversible oxidation at 0.84 V and irreversible oxidation redox couples at 1.27 V versus Ag/AgCl in acetonitrile solution, and reveal good stability of electrochromic characteristics, with a color change from yellowish to green at applied potentials ranging from 0.00 to 0.95 V.Structure and properties of PAI-2M (bottom left: cyclic voltammetry; bottom right: potential-step absorptometry).

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“…We attribute the unexpectedly low temperature for the glass transition of the triamine TPA-cured C0 sample to its nitrogen atom-centered core with three twistable p-toluidine groups, which increased the polymer's conformational flexibility or free volume and, consequently, lowered the value of T g . 23,24 Figure 4 reveals that the values of T g for the sets of epoxy resins followed the general trend B > C ¼ D > A. Typically, adding reactive modifiers to the epoxy increased the values of T g of the four systems, relative to those of the neat epoxies.…”

Section: Synthesis and Characterization Of Reactive Modifiersmentioning

confidence: 91%

Tailored thermal and mechanical properties of epoxy resins prepared using multiply hydrogen‐bonding reactive modifiers

Liu

Shau

Juang

et al. 2010

J of Applied Polymer Sci

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In this study, we synthesized a phosphoruscontaining triply functionalized reactive modifier, DOPOtris(azetidine-2,4-dione), and a phosphorus-free doubly functionalized reactive modifier, bis(azetidine-2,4-dione), and embedded them into epoxy resin systems. We characterized these synthesized reactive modifiers using Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, elemental analysis, and mass spectrometry. During the thermosetting processes, we reacted the epoxy curing agents 4,4-diaminodiphenylmethane and tris(4-aminophenyl)amine with the multiply hydrogenbonding reactive modifiers and epoxy monomers. The introduction of the DOPO segment, strongly hydrogen bonding malonamide linkages, and hard aromatic groups into the backbones of the synthesized reactive modifiers resulted in epoxy networks exhibiting tailorable crosslinking densities, flexibilities, glass transition temperatures, thermal decomposition temperatures, and flame retardancies. Furthermore, dynamic mechanical analyses indicated that intermolecular hydrogen bonding of these reactive modifiers enhanced the thermal and physical properties of their epoxy resins through the formation of unique pseudocrosslinked polymer networks.

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Synthesis and properties of new aromatic poly(amine‐imide)s derived from N,N′‐bis(4‐aminophenyl)‐N,N′‐diphenyl‐1,4‐phenylenediamine

Cited by 60 publications

References 18 publications

Synthesis and evaluation of photoluminescent and electrochemical properties of new aromatic polyamides and polyimides with a kink 1,2‐phenylenediamine moiety

Synthesis and evaluation of photoluminescent and electrochemical properties of new aromatic polyamides and polyimides with a kink 1,2‐phenylenediamine moiety

Poly(amine‐amide‐imide)s Bearing Pendent N‐Carbazolylphenyl Moieties: Synthesis and Electrochromic Properties

Tailored thermal and mechanical properties of epoxy resins prepared using multiply hydrogen‐bonding reactive modifiers

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